Indol-2-ylidene (IdY): Ambiphilic N-Heterocyclic Carbene Derived from Indole** |
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Authors: | Hyunho Kim Minseop Kim Dr Hayoung Song Prof Eunsung Lee |
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Institution: | Department of Chemistry, Pohang University of Science and Technology, Pohang, 790-784 Republic of Korea |
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Abstract: | The synthesis of ambiphilic N-heterocyclic carbene ligand, indol-2-ylidene (IdY, A ), is described. A series of indolenium precursors ( 2 a – f ) were prepared on a gram scale in good yields. Trapping experiments with elemental selenium, RhCl(cod)]2 and CuCl provided the expected carbene adducts. Further computational and spectroscopic studies supported the ambiphilicity of IdY, which lies between cyclic (alkyl)(amino)carbenes (CAAC-5) and cyclic (amino)(aryl)carbene (CAArC). The copper complexes ( 6 ) show high percent buried volume (% Vbur = 58.1) and allow for carboboration of terminal alkynes within 30 minutes in a demonstration of synthetic utility with good yields and high regioselectivity. |
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Keywords: | ambiphilic carbenes copper catalysis indoles ligand design N-heterocyclic carbenes |
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